EP0355541A2 - Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés - Google Patents

Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés Download PDF

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Publication number
EP0355541A2
EP0355541A2 EP89114518A EP89114518A EP0355541A2 EP 0355541 A2 EP0355541 A2 EP 0355541A2 EP 89114518 A EP89114518 A EP 89114518A EP 89114518 A EP89114518 A EP 89114518A EP 0355541 A2 EP0355541 A2 EP 0355541A2
Authority
EP
European Patent Office
Prior art keywords
sulfides
hal
polyarylene sulfides
poly
arylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89114518A
Other languages
German (de)
English (en)
Other versions
EP0355541A3 (fr
Inventor
Burkhard Dr. Köhler
Hans-Detlef Dr. Heinz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0355541A2 publication Critical patent/EP0355541A2/fr
Publication of EP0355541A3 publication Critical patent/EP0355541A3/fr
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02Polythioethers
    • C08G75/0204Polyarylenethioethers
    • C08G75/0286Chemical after-treatment
    • C08G75/029Modification with organic compounds

Definitions

  • the invention relates to high molecular weight polyarylene sulfides (PAS), preferably polyphenylene sulfides (PPS), made from polyarylene sulfides, preferably polyphenylene sulfide and dihalo compounds.
  • PAS high molecular weight polyarylene sulfides
  • PPS polyphenylene sulfides
  • Polyarylene sulfides known e.g. US-PS 3354129, EP-OS 171021. They are inert, high-temperature resistant thermoplastics, which also allow a high degree of filling with glass fibers and / or other organic fillers.
  • the use of these polymers, in particular polyparaphenylene sulfide (PPS), is increasing above all in areas that have hitherto been reserved for thermosets.
  • a disadvantage of PAS can be unsatisfactory toughness, which can increase with increasing melt viscosity. Rapid crystallization of the PAS can also be disadvantageous for some applications, for example in the production of films. The tendency towards rapid crystallization is also lower for PAS types with a high melt viscosity.
  • the invention therefore relates to high molecular weight polyarylene sulfides, preferably polyphenylene sulfides, prepared by reacting known polyarylene sulfides, preferably polyphenylene sulfide, with dihalogen compounds of the formula (I) Hal-R-Hal (I), in which R is C6 ⁇ 22-alkylene, preferably a hexamethylene, C6 ⁇ 22-cycloalkylene, C6 ⁇ 22-bis (halogenomethyl) arylene, the arylene radical preferably being an m- or p-phenylene radical or a 1,4-, 1st , 5-, 1,6-, 1,7-, 1,8-, 2,6- or 2,7-naphthylene and the arylene radicals can optionally be C1 ⁇ 6-alkyl, preferably methyl, halogen (e.g. Cl-, Br-) methyl-, C6 ⁇ 22- aryl, preferably phenyl or halogen (eg Cl
  • dihalogen compounds are aromatic and aliphatic dihalogen compounds of the formula (I), for example p-xylylene dichloride, m-xylylene dichloride, 2,4- (dichloromethyl) -1,5-dimethylbenzene, 1,6-dichlorohexane, 1,12-dichlorododecane, 1 , 2,3-, and 1,2,4- and 1,3,5-tri- (chlor methyl) benzene, 1,6- and 2,6-di (chloromethyl) naphthalene and the corresponding bromine compounds. They can be used individually or as a mixture.
  • the polyarylene sulfides are produced by melting together a mixture of polyarylene sulfide with 3 to 30% by weight, preferably 5 to 20% by weight, of dihalogen compound of the formula I, for example in (screw shafts) extruders, kneaders, etc.
  • An aftertreatment time in the melt is 0.5 to 500 min, preferably 5 to 60 min.
  • the suitable temperature for the aftertreatment according to the invention in the melt is 280 ° C. to 450 ° C., preferably 300 ° C. to 360 ° C.
  • moldings made from the polyarylene sulfides to be used according to the invention can also be after-treated with dihalo compounds of the formula (I) in the solid phase at from 150 ° C. to 270 ° C.
  • the process according to the invention can be carried out under inert gases (e.g. nitrogen, argon), if appropriate in vacuo up to 10 ⁇ 6 bar. Carrying out under inert gas is preferred.
  • inert gases e.g. nitrogen, argon
  • the polyarylene sulfides produced according to the invention can be processed into molded articles, fibers or films by the process of injection molding or extrusion.

Landscapes

  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
EP19890114518 1988-08-18 1989-08-05 Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés Withdrawn EP0355541A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3828058 1988-08-18
DE3828058A DE3828058A1 (de) 1988-08-18 1988-08-18 Hochmolekulare polyarylensulfide, hergestellt aus polyarylensulfiden und dihalogenaromaten

Publications (2)

Publication Number Publication Date
EP0355541A2 true EP0355541A2 (fr) 1990-02-28
EP0355541A3 EP0355541A3 (fr) 1991-01-30

Family

ID=6361122

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890114518 Withdrawn EP0355541A3 (fr) 1988-08-18 1989-08-05 Sulfures de polyarylène de poids moléculaire éléve, préparés à partir de sulfures de polyarylène et de composés dihalogénés

Country Status (4)

Country Link
US (1) US4978729A (fr)
EP (1) EP0355541A3 (fr)
JP (1) JPH02103233A (fr)
DE (1) DE3828058A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991008249A1 (fr) * 1989-11-17 1991-06-13 Eastman Kodak Company Procede de preparation de copoly(arylene sulfure) presentant une quantite diminuee de radicaux de disulfure
EP0524827A1 (fr) * 1991-07-24 1993-01-27 Kureha Kagaku Kogyo Kabushiki Kaisha Procédé pour la préparation de copolymère de polysulfure d'alkylène d'arylène
US8883960B2 (en) 2007-01-04 2014-11-11 Sk Chemicals Co., Ltd. Polyarylene sulfide resin with excellent luminosity and preparation method thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022030459A1 (fr) * 2020-08-05 2022-02-10 株式会社クレハ Résine de sulfure de polyphénylène modifié, composition de résine, et article moulé

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3524835A (en) * 1963-11-27 1970-08-18 Phillips Petroleum Co Heat treatment of poly(arylene sulfide) resins
US3395132A (en) * 1967-01-23 1968-07-30 Dow Chemical Co Method for crosslinking polyphenylene sulfide resins
US3607843A (en) * 1969-05-16 1971-09-21 Phillips Petroleum Co Process for making poly (phenylene sulfide) polymers of increased molecular weight
US3839301A (en) * 1973-07-23 1974-10-01 Phillips Petroleum Co Poly(arylene sulfide) resin heat treatment and curing
US4645826A (en) * 1984-06-20 1987-02-24 Kureha Kagaku Kogyo Kabushiki Kaisha Process for production of high to ultra-high molecular weight linear polyarylenesulfides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991008249A1 (fr) * 1989-11-17 1991-06-13 Eastman Kodak Company Procede de preparation de copoly(arylene sulfure) presentant une quantite diminuee de radicaux de disulfure
EP0524827A1 (fr) * 1991-07-24 1993-01-27 Kureha Kagaku Kogyo Kabushiki Kaisha Procédé pour la préparation de copolymère de polysulfure d'alkylène d'arylène
US5605987A (en) * 1991-07-24 1997-02-25 Kureha Kagaku Kogyo K.K. Production process of alkylene thioether-arylene thioether copolymer
US8883960B2 (en) 2007-01-04 2014-11-11 Sk Chemicals Co., Ltd. Polyarylene sulfide resin with excellent luminosity and preparation method thereof
US8957182B2 (en) 2007-01-04 2015-02-17 Sk Chemicals Co., Ltd. Polyarylene sulfide resin with excellent luminosity and preparation method thereof

Also Published As

Publication number Publication date
EP0355541A3 (fr) 1991-01-30
DE3828058A1 (de) 1990-02-22
JPH02103233A (ja) 1990-04-16
US4978729A (en) 1990-12-18

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